Oxazolidines and a method of preparing the same



Patented Aug. 16, 1949 PREPARING Jack T. Thurston, Riverside,- Gonm,assignortto; "American Cyanamid Company," New; York;

N. Y., a corporation of-MaineP No Drawingpplicatioml Serial No. 642,937

12 Claims; l The present invention relates to oxazolidines and to amethod'for their preparation.

The oxa zolidines of the present invention; are- 2-imino-3-substitutedoxa-zolidines which. may. be nephew:ntediby"theifpllmvinxzstmcturalAtormul Rem-Q B FI 15H? when im be anvlinhei alawl l an e s adies! T e, exez i' ne l' a e He eoarei y.reacting, o, y id w t a e on a ymn efli e elam i enerati nmule, v v y vt where Bimaybelanwofrzthe aforementioned raii- 'liheusual reaction of;ai cyanogzenhalide with an amine islthe formation: of" substitutedcyanamides; I'tz'is;showmirr:UnS, .Patent5N0 253,551,671 that the'reaction of a monoalkylol; amine: wth' a cyanogen halide yields analk-ylol Qy mamida From. thisiti would be expected that: azsecondarymonoalkylolamine:wouldv'yilchadisubstituted cw anamideupon reaction:with; a cyanogen halide; However, it: has: been. discovered that:reaction o a cyanogen halide with secondary monoethanol amines resultsin cyclization with the formation of the heterocyclic2-imino-3-substituted oxazolidines.

Generally, the reaction proceeds readily, ordinary temperatures of theorder of ropmrtmlierar ture or slightlyabove being suflicient. However,in some cases higher temperatures and pressures are requiredbutsuchareto be avoided because of side-reactions. Began of theexotl ermicnature and rapidity of thereaction external cooling is generallyemployed to permit the cyanogen halide tabs ntr du ia a t o a e Thereaction is ,most conveniently carried out in a solvent; an'inertsolverrt such as "benzene, hexane, and the like, being preferredalthough a hydroxylic solvent such' as ethanol, iso-propanol', and thelike, may also be employed but is less desirable because f" the presenceof the hydroxyl group in the molecule. Likewise, while solvents Lcontaining appreciable proportions: of water may be used, this "shouldbeavoid'ed since adecrease in yieldresults.

" As aforementioned; the substituent replacing one of theN hydrogen'sofmonoethanol amine to provide an N-substituted mpnoethanolamine, i. e., asecondary monothanolamine, may be any aliphatic, aralkyl, aryl,or-ali'cyclic radical.

The cyanogen halide, generally the chloride or bromide but preferablythe chloride, may be added 0 th rea tio mixtl f ei h as a liquid as agasintroduced above or below the surface or the reaction mixture, ordissolyedin a solvent such asbenzene, hexane, C014 and the likl Theoxazolidines of the present invention, are

useful as insecticides-and chemical intermediates;

in the production of pharmaceutical and chemol te s a e ri l and l sineagents, resinsgplasticsgandthelike. In many c ases's lts W i I m be.lit-sn red brot e 'ne h o zlb idi'l'ie with acidic materials such asHCIjHzSOi, H3304 acetic acid, rzropionic acid, phen l Q 2 hfi l m o edih WmoI hefi c; oxazolii dine. n; following,exa nnlessh wih pr pa a onofvarious f ami e- A u stituted qxe z ll n s by meansofwthe rocess of hpresentinven EXAMPI-il; 1 2 imino-J-phenylosqazolidine 1 1-N=0\ /CH:

Reagents Molar Ratio Phenylthanolamino 120 Benzener n ud V 1.0Cyanogenchlorid The phenyl'ethanolamine, is dissjolved in the benzene,and the resulting solution is cooled to 10 C. Cyanogen chloride ispassed in slowly as the reaction is strongly exothermic. The temperatureis kept below; substantially 5 C., both by adjusting theaddition rateofthecyanog'en chloride and. also by the application; .of externalcooling; The reaction is hefi il carried out in a flask provided with a'reflux condenser through which is circulated Water sufliciently cold: tocondense. any mana r; hlo devapors that this: reactant is returned:tozth. reaction vessel. When the-.additionof the: cyanogenchloride hasbeen: comp1e ed-,. t e external cooling is terminated; and the; reaction'mixture; agitated until; exothermic: tendencies ,areno loner-evidenced. It, may be-neoessary'to, apply occasignal cooling forasnort-t me a r aa cl ti 2 19fithe amount to an aqueous solution of thehydrochloride salt. The free base precipitates and after filtering,washing with water, and drying, it melts at 99-100 C. The free base isrecovered quantitatively from the hydrochloride salt.

EXAMPLE 2 2-imino-3-butyloa:azolidine The butylethenolamine is dissolvedin the hexane, and the resulting solution is cooled to 5 C. by means ofexternal cooling. The solution of cyanogen chloride in benzene is addedslowly to the agitated reaction mixture, so that the temperature doesnot exceed 30 C. During the reaction the mixture separates into twoliquid phases, and after the addition of cyanogen chloride is completed,the mixture is first stirred at room temperature for about 45 minutesand then at -50 C. for about minutes. The light brown oily phase isseparated from the hexane-benzene solution and dissolved in water toform an aqueous solution. This solution is treated with an excess of 10%sodium hydroxide until the pH is 9-10, and extracted several times withether. After combining and drying the ether extracts, the ether isremoved by distillation and 2-imino-3-butyloxazolidine, boiling at 74-75C./3 mm., is distilled from the remaining residue. The hydrochloridesalt may be prepared by adding HCl gas to a benzene solution of2-imino-3-butyloxazolidine until a slight excess of the acid is present.Filtration of the precipitate yields a colorless crystalline solid whichmelts at 145147 C.

Reagents Molar Ratio Butylethanolamine 1.0 Cyanogen chloride 1.0 Sodiumhydroxide- 1.0 Benzene 7. 9

tained at 5-15 C. After the addition of the cyanogen chloride iscompleted, the reaction mixture is stirred at room temperature for about2 hours. The sodium chloride which is formed during the reaction isremoved and washed with several small portions of benzene. Aftercombining the washings and the filtrate the benzene is removed undervacuum leaving an oily residual liquid which is purified by distillationto yield 2-imino-B-butyloxazolidine boiling at Hf- C./3.mm.

EXAMPLE 3 Reagents Molar Ratio Dodecylethanolamine Hexane Cyanogenchloride The hexane solution of dodecylethanolamine is cooled to 10 C.which causes some of the amine to precipitate. To this agitated slurryis then added the cyanogen chloride, either dropwise or as a gas. Thereaction becomes exothermic, and the temperature is allowed to rise toabout 35-40 C., which is substantially the temperature maintained duringthe addition of the cyanogen chloride. After addition is completed, thereaction mixture is stirred until the temperature drops spontaneously to2025 C. The crystalline waxy 2-imino-3-dodecyloxazolidine hydrochlorideis recovered, and after recrystallization from benzene the product meltsat 161- 162 C.

To obtain the free base the hydrochloride of2-imino-3-dodecyloxazolidine is dissolved in water and treated dropwisewith the stoichiometric amount of 10% aqueous sodium hydroxide. Aninsoluble oil, 2-imino-3-dodecy1oxazolidine,

separates, and after being extracted with ether,

the ethereal solution is dried over anhydrous sodium sulfate. The etheris removed and the residue, 2-imino-3-dodecyloxazolidine, is not furtherpurified because it is unstable at the temperatures required fordistillation.

Molar Ratio Reagents Diroo The dodecylethanolamine, the sodiumhydroxide, preferably in powdered form, and the benzene are mixed andthoroughly agitated. The cyanogen chloride is added to this agitatedmixture at a rate of substantially 2 mols per hour. During reaction thetemperature is maintained at 5-15 C. After the cyanogen chlorideaddition is completed, the reaction mixture is stirred at roomtemperature for about an hour. The sodium chloride which forms duringthe reaction is removed, and the clear yellow benzene solution may beconcentrated to yield the waxy free base, crude2-imino-3-dodecyloxazolidine. However, since this material is moreeasily recovered as hydrochloride, the aforementioned yellow benzenesolution is best treated with approximately a stoichiometric amount. of.gaseous HCl at a temperature range of 5"-'30"' C. After removing thebenzen'e undenvacuum. the crude waxy hydrochloride salt is digested withboiling acetone, the solid is filtered; andwashed with cold acetone.Additional impurities can be removed by a second digestion in hotacetone. The crystalline 2-imino-3-dodecyloxazolidine hydrochloride obind the e om me ts at .l.. .2 C.-

EXAMPLE .4: Z-iim'no-Zl cyelohemyloxazolidihe CH2CH2.

I Re ents ;Molar Ratio gyclolierylethanolami'ne. 2 soul 1; o Benaene 6.5

The. slurry of. cyelohexylethanolamine and.jsodiumhydroxide, preferably.in powdered ilorm is agitatedand. cooled to C..while the cyano en.chloride. is. added at the. 'rate of one moi er 45:65 minutes..'D'uri'ng reaction the temperaturelis allowed. tori'se slowly to about1:5 C .,an.d'l.after the addition oi the cyanogen ramme; completed, the.reaction mixture. is stirred for about 3 hours at approximately 30 C.The sodium chloride formedduring the reaction is removed and washed withbenzene. The benzene washingsand the filtrateare combined and thebenzene removed under. reduced pressure.

The residue is crude 2-imiho-3-cyclohexyloxazolidine which is distilledat; 115 116 C./3 mm. The hydrochloride-saltmaybe prepared by treatingthe free base with approximately a stoichiometric amount ofHCl. Afterthis colorless solid isrecovered-and dried it melts at l9'7--1%8- 6.

may be desirable to recover the 2-imino-3- cyclohexyl'oxazolidine asthe-hydrochloride with-- out resorting. to. the. above mentioned: vacuumdistillation: In' this case the benzenefiltrate; containing. thefreebasa. is. treated with gaseous HCl. precipitating colorless-2-imino-3-cyclohexyloxazolidiner hydrochloride which: melts,

The octadecyle'thanolamine is dissolved in the benzene and:,. thesodiumhydroxide, preferably in powdered form; isadded tothis solution.This stirred .mix-ture i-szcooled to approximately 1 5 6.; andpthecyanogen chlonide addition: is started-iv During reaction thetemn ratureis allowed :torise to ubstantially 30 .C. an h addition rat fl the cyann hl i e em proximately one moi per..30 minutes. After the addition ofthe cyanogen chloride is completed, the: reaction mixture stirnedlat-2(l-30 (SJ-for 1-2 hours. The gelatinous sodium chloride which formsduring the reaction is removed by means of a centrifuge andwashedwithseveral small portions of benzene. The filtrate and washings containing2 -imin'o- 3 octadecyloxazolidine are combined and cooled tosubstantially 5 C. A slight excess of gaseous hydrogen chloride over thetheoretical amount required is added at a of'about 2.5 mols an hour, andthe temperature is maintained below 25 C: Removal of the benzene andanyexcesshydrogen chloride under reduced pressure leaves a waxy residue.of 2 imino 3 octadecyloxazolidine. hydrochloride which is then digestedin boiling acetone for approximately 3ominutes mixtureis; thencooledatoiilf ltl C }.,..th e solid filtereiwashediwith cold. acetone,and: dried. Purification of 2--.- iinino 3.--octadecyloxazolidine.hydrochloride may also be accomplished by crystallization. from ethanoland/ or from a mixture. of: acetoneand benzene. The. melting, point. of.the purified .hy. drochloride. salt. of 2.-imino-3.-oetadeeyloxazoliadineis 9.3-9.5 C. The freebase be: isolated byevaporating the originalbenzene. solution. ob,-' tainediafter theremoval.ofsodiurrrchloride-from the reaction. mixture. The.2-iminQr3-06tadecyloxazolidine so obtained is a gummy Waxy materialwhich may also be prepared by the additionof substantially astoichiometric amount of. sodium hydroxide.- to a solution .of. the:hydro-- chloride saliz.

Eximnirfl' 2-imino-3-5-carbqmylethylowazolidine C Hz Reagents MolarRatio fl-Carbamylethylethanolamine. i=0 Cyanogen chloride 1. 0Sodiun'rethoxide l. 0 Ethanol 7. 6

The fl-carbamylethylethanolamine is dissolved in about one-halfoitheaboveamountoi ethanol,. and the solution cooled to about 0-5 C. Thecyanogen chloride then added at .therate: of approximately one. mol: per2. hours. while. the temperature is kept below substantially 15*? C, Thesodiumethoxide dissolved in. the remaining. amount-of he hovez nisaddmit ihismact-1on mixture to. neutralize the HCl formed. During thisaddition. .the temperature: is. not al.- lowed to rise aboveapproximately 30 C., and the. rea t on mixtu is hei ei for 1- mi Thesodium chloride which is formed is then removed-..by filtration, and theresultant clear filtrate is evaporated-to.drynessatreduced pres,-sure-to. yield crude. 2-imino-3-p-carbam-ylethyloxazolidingel. In order.torernove some impurities from. this crude 2eimino-3- B-carbamy1ethyl,-oxazolidine,,.it is. digested. in boiling. ethanol, cooled -filtered andwashed with a. small amount of fresh, coldi ethanol. 2.-imino 3 3.carbamyl.- ethy loxazolidine. may also. be recrystallized. from aqu oust anolv to yield colorles n s melting at 191)? 7 EX MPLE 7 2-imino-3p-sulfonamidophenyloxazolidine Ethanol, absolute Cyanogen chloride isadded rapidly to the alcoholic solution of thep-sulfonamidophenylethanolamine at substantially 45 C. Only a slighttemperature rise occurs and after addition the reaction mixture isstirred for 30-60 minutes, before it is allowed to cool slowly to roomtemperature. A slight amount of insoluble material is removed byfiltration, and the clear alcoholic filtrate is concentrated undervacuum giving a residue of crude 2 amino 3 psulfonamidophenyloxazolidine hydrochloride which, afterrecrystallization from alcoholic acetone, melts at 1689 -171 C.

The free material, 2-amino-3-p-sulfonamidophenyloxazolidine may beobtained by adding substantially a stoichiometric amount of sodiumhydroxide or sodium ethoxide to the above alcoholic filtrate, removingthe resultant sodium chloride, and isolating the substitutedoxazolidine.

EXAMPLE 8 Z-z'mino-3-p-bromophenyloxazolidine B IOIIT C Ha Thep-bromophenylethanolamine is dissolved in benzene and this solution isheated to approximately 60 C. The cyanogen chloride is added to thisagitated reaction mixture at the rate of approximately 0.6 mol per hour.The temperature rises only slightly during the addition of cyanogenchloride. After the addition of the cyanogen chloride is completed thesolution becomes cloudy and is stirred and heated at substantially 60-65C. for about 3 hours. On cooling, crystals of 2 amino 3 pbromophenyloxazolidine hydrochloride separate which after filtering,washing, and drying melt at 143145 C.

The free base, 2 amino 3 p bromophenyloxazolidine, may be prepared bythe addition of approximately a stoichiometric amount of 10% aqueoussodium hydroxide to an aqueous solution of the hydrochloride salt. Afterfiltering the precipitate and crystallizing it from an ether-heptanesolution, the purified 2-amino-3-p-bromophenyloxazolidine melts at114=-115 C.

Exemm 9 2-imino-3-p-chlorophenyloxazolidine HN=C\ /CH1 Reagents MolarRatio p-Chlorophenylethanolamine l. 0 Cyanogen chloride l. 3 Benzene 9.7

The p-chlorophenylethanolamine is dissolved in the benzene and thesolution heated to about 45 C. The cyanogen chloride is then added atthe rate of 0.6 to 0.7 mol per hour. During reaction the temperaturerises about 10 C. and the solution becomes cloudy before the cyanogenchloride addition is completed. The reaction mixture is stirred about anhour at approximately 50 0., and then allowed to cool slowly.Crystalline 2-imino-3-p-chlorophenyloxazolidine hydrochloride separates,which after filtering, washing with benzene, and drying melts at -146 C.Addition of substantially a stoichiometric amount of aqueous sodiumhydroxide to an aqueous solution of the hydrochloride salt precipitatesthe free base. The free base is recovered, and after recrystallizationfrom ethereal hexane, the 2 imino-3-p-chlorophenyloxazo1idine melts at97- 98 0.

EXAMPLE 10 2-imino-3-butyl-5-phenyloasazolidine C4HQNCH1 The2-phenyl-2-butylaminoethanol-1 is dissolved in the benzene, and thesodium hydroxide, preferably in powdered form, is added to thissolution. The resultant agitated mixture is cooled to approximately 5 C.and the cyanogen chloride added at the rate of approximately one mol perhour, during which time the temperature is not allowed to rise aboveabout 25 C. When the cyanogen chloride addition is complete, thereaction mixture is stirred at room temperature for approximately anhour, and the sodium chloride which forms during the reaction, is thenremoved and washed with small portions of benzone. The washings andfiltrate are combined, and the benzene removed under reduced pressure,yielding a residue of crude 2-imino-3-butyl-5- phenyloxazolidine, whichis a straw colored oily material that does not crystallize readily. Thisoily material is redissolved in benzene, and the solution treated withan amount of dry gaseous hydrogen chloride slightly in excess of thetheoretical requirements while the temperature is maintained atapproximately 0-5 C. On standing, 2-imino-3-butyl-5-phenyloxazolidinehydrochloride crystallizes from the benzene solution.

After? recovery? crystallizatiornfromv l methaw noliw acetonextfimhydrochloridei melts att-14&'- 149 C.

The fi-N-octadecylcarbamylethylethanolamine, the sodium hydroxide:preferaloly powdered form, and the benzehesare:mixediandtthorouglilyagitated. The cyanogenrchloride isladdedito the mixture at therateoffapprbxhnately L: m'ol's per hour;v while: the temperature: is keptbelow about 35 C; After the ad'dition. of'the cyanogen: chlo:-- ride'ziscompletedgzthe; mixture? i'szstirre'd for) about amhounatflfi w c.'llheisodiumehlorideiwhick forms-duringthis-reactioniisremovedhyfiltration: and: washed with. sevrafsmailrportionsr'ofi' hens zene. The combined washings and filtrate are cooledto about 5 C. This solution containing Z-imino 3-(B-N-octadecylcarb'amyDethoxazolidine is stirred while a slight excess of gaseous hydrogenchloride over. the theoreticalqamount required added in about two"hours-l. The benF- zene is removed under reduced press-urep-a-nd thesticky residue of: crude 2-+i1 nino-3'--(B-N-oct-adecylcarbamyl)ethyloxazolidine hydrochloride is diboiling-acetone for about an'hour, then cooled tom- C; After filtering underpressurethe; solid- ;iswa shed= with small portions of fresh,-coldacetone to yield slightly impure. 2-imino53 (fi-N-octadecylcarbamyl)ethyloxazolidine hydrochloride melting at 139 -140" C.

The free base 2-i'mino-3-(fl N-octadecylcarbamyl) -ethyloxazolidine, maybe prepared by treating the hydrochloride salt with approximately astoichiometric amount of. sodium hydroxide After'rei'rioval"o'ftliesodiu'm' chloride free Base" is a sticky gummy products 12z-im'iizb-s (p zv-neeadecyreoibmyzi emmoxazolidine" i" CloIfu'-N=-G'-'GH+-GHz- N -''-GH BN5 CH5' 0 Reagents"; fiolanfiatiofl-Ndfexadcylbafliarnylethylethanolamine- 1. o Cyanogen chloride. 1. 0Sodium hydroxide- 1. 0 Benzene 17.0

The procedure for preparing"2 imino-3 GB N hexsaeeyicatbamyn ethylexazonuiae is substantially the same as that reported in Example 11. Thecyanogen chloride is added to the benzene slurry of the5-N-hexadecylcarbamylethylethanolamine and sodium hydroxide, preferablyin powdered form, at a rate of about one mol per I8 hour-1' During."reaction the: temperature 'is' not allowed tol ris'e' aboveapproximately-30 C. After the: completion of: the addition of: the:cyanogen clilorid'e', the reaction mixture is stirred at: room%,

'1 temperature: fon'abouti Zihours: Afterremoval of the: sodium?chloride formed. during' thek reaction, the benzene? filtrate: istreated with substantially a stoiohi'ometrio amount of gaseous hydrogen.chl'oridEin-a temperature range 0f1'09-10" C. and? the benzene: solutionconcentratedi at: reduced pressure: to" yield crude 2:-imino-3= (fl 'Nh'exa decylcarbamyllr ethy-Ioxazolidiner hydrochlorldez. purification;the:-- crude-hydrochloride: is di gested inia'cet-one'; filtered; anddried toiyie'ldi'a waxysolidz: The freebase maybe prepared by 'theaddition. of astoichiometricia'mount of aqueoussodium 'hydrroxide to:the hydrochloride saltto: obtain a sticky oily material.

The procedure fpllowediin thepreparation ct 2' 'imino=-- 3 v (fl-Ntetradecylcanbamyl) ethyloxe azolidineis essentially the sameasathatreported 1 in- Example 11. The: cyanogen chloride is; added. to.-thebenzene-slurry of the o-N-tetradeeylcart-- be. myvlethylenethanolamineand: sodium' hydrox ide preferably in; powdered form; at ai rates'ot" 1;O-1.=.5 mols per houp'whiley the" temperature maintained below l C.After additiQn;,thB'l-- actionmixture is' stirred fox-about an: hour-The sodiumrchloride, whichionms;duringthe reactiorr:

is removed and approximately a stoichiometric amount of gaseoushydrogenchlo ride addedaat a temperature range 7 on 0 -10 C. The:- benzene is.removed at reduced pressure to yieldpa: tan

ethyloxaaolidine hydrochloride. The free :base, prepared by treating.-the hydrochloridewitlnan: equiyalent or sodium.- hydroxide is: a stick-yoily material.

B-N-D ode cylcarhamylethyle thanolamine Cyanogenchlorid'eSodium'hydloxide Benzene .c

The procedure for preparing 2-imino-3-(p-N- dodecylcarbamyl)ethyloxazolinide is substantially the same as that described in theabove examples. The cyanogen chloride is added to the benzene slurry ofthe p-dodecylcarbamylethylethanolamine and sodium hydroxide, pref-'Treatment of the hydrochloride with a stoic-himetric amount of aqueoussodium hydroxide yields the free base in the form of a viscous oil.

EXAMPLE 15 2-imino-3-ethylo:cazolidine CzH N--(|JH HN=C\ /CH2 ReagentsMolar Ratio Ethylethanolamine l. 00 Cyanogen chloride l 1.00 Sodiumhydroxide. 1.05 Benzene... 5.60

The agitated benzene slurry of ethylethanolamine and sodium hydroxide,preferably in nowdered form, is cooled to about 5 C., and the cyanogenchloride is added to this agitated reaction mixture at'the rate of onemoi per 60-75 minutes, while the temperature is allowed to reach 20-25C. Stirring is then continued for about 2 hours, and the temperature isallowed to reach 30-35 C. The sodium chloride which is formed in thereaction is removed by filtration and washed with benzene. The combinedwashings and filtrate are concentrated under reduced pressure.Distillation of the residue yields 2-imino-3-ethyloxazo1idine boiling at5960 C./3 mm.

The N -substituted ethanolamines which are not commercially availableand which are used as reagents in the present invention are readilyprepared by simple and straightforward known chemical methods. Several.of the substituted ethanolamines are prepared by the reaction ofethylene oxide with a primary amine. Ethanolamines, similar to that usedin Example 10, are

prepared by reacting a substituted ethylene oxide with a primary amine.The fi-carbamylethylethanolamine used in Example 6 is prepared by thecareful addition of a stoichiometric amount of acrylamide toethanolamine while the temperature is maintained high enough to insure aclear melt. When this melt is cooled to room temperaturethe crude solidfi=carbamylethylethanoh amine is used without further purification. Thepreparation of the B-N-substituted-carbamylethylethanolamines which areused in Examples 11-14 involves several steps. A stoichiometric amountof ethanolamine is carefully added to ethyl acrylate. The resultingethyl hydroxyethylp aminopropionate is then treated with eitherdodecylamine, tetradecylamine, hexadecylamine,

or octadecylamine at approximately C. to produce the desiredp-N-substituted-carbamylethylethanolamine. A theoretical amount ofethanol is distilled from this reaction mixture. 7 When cooled to roomtemperature a waxy solid is obtained, and these p-N-substitutedcarbamylethylethanolamines are used in Examples 11-14 without furtherpurification.

While the invention has been described with particular reference tospecific embodiments, it is to be understood that it is not to belimited thereto but is to be construed broadly and restricted solely bythe scope of the appended claims.

I claim:

1. A 2-imino-3-substituted oxazolidine, 3-substituted radical being amember selected from the group consisting of alkyl, aryl, aralkyl' andcycloalkyl radicals.

2. A 2-i1nino-3-phenyl oxazolidine.

3. A 2-imino-3-alkyl oxazolidine.

4. 2-imino-3-phenyl oxazolidine.

5. 2-imino-3-butyl oxazolidine.

6. 2-imino-3-dodecy1.oxazolidine.

7. A method of preparing a 2-imino-3-substituted oxazolidine. said3-substituted radical being a member selected from the group consistingof alkyl, aryl, aralkyl and cycloalkyl radicals com-.

prising reacting a cyanogen halide with a secondary monoethanolaminehaving the formula Hz in wherein R. represents a radical selected fromthe group consisting of alkyl, aryl, aralkyl, and cycloalkyl radicals.

8. A method of preparing a 2-imino-3-substituted oxazolidine, saidS-substituted radical being a member selected from the group consistingof alkyl, aryl, aralkyl and cycloalkyl radicals corn prising reactingcyanogen chloride with a secondary monoethanolamine having the formulaE2 H2 R1|\ o-corr wherein R represents a radical selected from the groupconsisting of alkyl, aryl, aralkyl, and cycloalkyl radicals.

9. A method of preparing a 2-imino-3-phenyl oxazolidine comprisingreacting cyanogen chloride with an N -pheny1 monoethanolamine.

10. The method of claim 9 in which the reaction is carried out in ahydrocarbon solvent at a temperature in the approximate range of 0-60 C.

11. A method of preparing a Z-imino-B-alkyl oxazolidine comprisingreacting cyanogen chloride with an N -alkyl monoethanolamine.

12. The method of claim 11 in which the reaction is carried out in ahydrocarbon solvent at a.

-temperature inthg approximate range of 060 C.

JACK 'r. THURSTOIQ REFERENCES CITED The following references are ofrecord in the file of this patent:

Chemical Abstracts, vol. 26, page 2168 (1932). v

said

